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RESEARCH PAPER · Angewandte Chemie International Edition · 2018

High Throughput Strategies for the Discovery and Optimization of Catalytic Reactions

Eric S. Isbrandt, Ryan J. Sullivan, Stephen G. Newman

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High Throughput Strategies for the Discovery and Optimization of Catalytic ReactionsOriginalRapid route design of AZD759420Role of continuous flow processes in green manufacturing of pharmaceuticals and specialty chemicals71Discovery and Comparison of Homogeneous Catalysts in a Standardized HOT‐CAT Screen with Microwave‐Heating and qNMR Analysis: Exploring Catalytic Hydration of Alkynes5Autonome Entdeckung in den chemischen Wissenschaften, Teil I: Fortschritt12Autonomous Discovery in the Chemical Sciences Part I: Progress317Reductive Arylation of Arylidene Malonates Using Photoredox Catalysis47High-Throughput Discovery and Evaluation of a General Catalytic Method for N -Arylation of Weakly Nucleophilic Sulfonamides32Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications192Accelerated Discovery in Photocatalysis by a Combined Screening Approach Involving MS Tags9Machine Learning for Catalysis Informatics: Recent Applications and Prospects613High-throughput screening of organic reactions in microdroplets using desorption electrospray ionization mass spectrometry (DESI-MS): hardware and software implementation51Exploring Homogeneous Conditions for Mild Buchwald–Hartwig Amination in Batch and Flow51A Perspective on Innovating the Chemistry Lab Bench17Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids**237Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids**32Comprehensive online multicolumn two-dimensional liquid chromatography-diode array detection-mass spectrometry workflow as a framework for chromatographic screening and analysis of new drug substances19Reaction Cycling for Kinetic Analysis in Flow17Droplet Precise Self‐Splitting on Patterned Adhesive Surfaces for Simultaneous Multidetection20Droplet Precise Self‐Splitting on Patterned Adhesive Surfaces for Simultaneous Multidetection104Identification of efficient promoters and selectivity trends in high temperature Fischer-Tropsch synthesis over supported iron catalysts89From molecular catalysts to their incorporation in porous materials : the case of regiospecific aromatic CH arylation0Reactive Extraction Enhanced by Synergic Microwave Heating: Furfural Yield Boost in Biphasic Systems32High-Throughput Experimentation in Olefin Polymerization Catalysis: Facing the Challenges of Miniaturization45Multidimensional Classification of Catalysts in Oxidative Coupling of Methane through Machine Learning and High-Throughput Data30Using Ligand-Accelerated Catalysis to Repurpose Fluorogenic Reactions for Platinum or Copper24A Widely Applicable Dual Catalytic System for Cross-Electrophile Coupling Enabled by Mechanistic Studies68Disulfonated xantphos for mass spectrometric mechanistic analysis4Bridging Lab and Industry with Flow Electrochemistry168Iterative Supervised Principal Component Analysis Driven Ligand Design for Regioselective Ti-Catalyzed Pyrrole Synthesis39Catalysis-Based Fluorometric Method for Trace Palladium Detection with Improved Convenience7Regio-selectivity prediction with a machine-learned reaction representation and on-the-fly quantum mechanical descriptors169Lipids as versatile solvents for chemical synthesis12Synchrotron infrared spectroscopic high-throughput screening of multi-composite photocatalyst films for air purification4The influence of additives on orthogonal reaction pathways in the Mizoroki–Heck arylation of vinyl ethers4Toward Machine Learning-Enhanced High-Throughput Experimentation155Recent progress in high-entropy alloys for catalysts: synthesis, applications, and prospects275Reaction screening in multiwell plates: high-throughput optimization of a Buchwald–Hartwig amination47A Perspective on the Analytical Challenges Encountered in High-Throughput Experimentation57Titanium Complexes with Functional Alkoxido Ligands for Selective Ethylene Dimerization – A High Throughput Experimentation Approach6Standardized Stirring for Small Scale Surveys**0Advancement in Organic Synthesis Through High Throughput Experimentation41Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis36Unveiling Organocatalysts Action – Investigating Immobilized Catalysts at Steady‐State Operation via Lab‐on‐a‐Chip Technology12Chemputation and the Standardization of Chemical Informatics73Tandem C–O and C–H Activation at Palladium Enables Catalytic Direct C–H Alkenylation with Enol Pivalates0Front Cover: Unveiling Organocatalysts Action – Investigating Immobilized Catalysts at Steady‐State Operation via Lab‐on‐a‐Chip Technology (ChemCatChem 24/2021)0Shortening Synthetic Routes to Small Molecule Active Pharmaceutical Ingredients Employing Biocatalytic Methods264Direct Synthesis of Light Olefins Using CO and CO2 Hydrogenation Reactions0High-Throughput Experimentation in Organometallic Chemistry and Catalysis5A reactivity model for oxidative addition to palladium enables quantitative predictions for catalytic cross-coupling reactions63An integrated resource-efficient microfluidic device for parallelised studies of immobilised chiral catalysts in continuous flow via miniaturized LC/MS-analysis7Recent development in machine learning of polymer membranes for liquid separation31Merging Late-Stage Diversification with Solid-Phase Peptide Synthesis Enabled by High-Throughput On-Resin Reaction Screening19Machine learning studies on asymmetric relay Heck reaction—Potential avenues for reaction development20Multistage Nucleic Acid Amplification Induced Nano-Aggregation for 3D Hotspots-Improved SERS Detection of Circulating miRNAs1GraphRXN: A Novel Representation for Reaction Prediction0Palladium-Catalyzed Direct C–H Alkenylation with Enol Pivalates Proceeds via Reversible C–O Oxidative Addition to Pd(0)14Multistage nucleic acid amplification induced nano-aggregation for 3D hotspots-improved SERS detection of circulating miRNAs31Using Active Learning to Develop Machine Learning Models for Reaction Yield Prediction26High‐Throughput Platform for Novel Reaction Discovery6Ultrahigh Loading Copper Single Atom Catalyst for Palladium-free Wacker Oxidation7Current Outlooks on Machine Learning Methods for the Development of Industrial Homogeneous Catalytic Systems3Development of Advanced High Throughput Experimentation Platforms for Photocatalytic Reactions5High-Throughput Synthetic Chemistry in Academia: Case Studies in Overcoming Barriers through Industrial Collaborations and Accessible Tools3Synthesize in a Smart Way: A Brief Introduction to Intelligence and Automation in Organic Synthesis1Ligand‐Promoted Catalysed Reactions0Evolution of design approaches in asymmetric organocatalysis over the last decade5High-Throughput Experimentation, Theoretical Modeling, and Human Intuition: Lessons Learned in Metal–Organic-Framework-Supported Catalyst Design25Electrochemical Carbon-Ferrier Rearrangement Using a Microflow Reactor and Machine Learning-Assisted Exploration of Suitable Conditions18High‐Throughput Experimentation as an Accessible Technology for Academic Organic Chemists in Europe and Beyond**32A Brief Introduction to Chemical Reaction Optimization437High‐Throughput Diversification of Complex Bioactive Molecules by Accelerated Synthesis in Microdroplets31High‐Throughput Diversification of Complex Bioactive Molecules by Accelerated Synthesis in Microdroplets8Quantitative benchtop 19F NMR spectroscopy: a robust and economical tool for rapid reaction optimization0Virtual Ligand Strategy in Transition Metal Catalysis Toward Highly Efficient Elucidation of Reaction Mechanisms and Computational Catalyst Design27Homogeneous, heterogeneous, and enzyme catalysis in microfluidics droplets24Deoxygenative Suzuki–Miyaura arylation of tertiary alcohols through silyl ethers21Robotic platform for accelerating the high-throughput study of silver nanocrystals in sensitive/selective Hg2+ detection15Interweaving catalysis and cancer using Ru- and Os-arene complexes to alter cellular redox state: A structure-activity relationship (SAR) review30Rapid Identification of Enamine‐based Organocatalysts for Quaternary Carbon‐containing Aldol Reactions via Fluorescence‐based Screening0Recent Progress on One-Pot Multisubstrate Screening16Legion: An Instrument for High-Throughput Electrochemistry48A deep learning framework for accurate reaction prediction and its application on high-throughput experimentation data46Introduction to High‐Throughput Experimentation (HTE) for the Synthetic Chemist11Development of high‐throughput wet‐chemical synthesis techniques for material research38Nickel-Catalyzed Transesterification of Methyl Esters0Palladium‐Catalyzed Combinatorial Synthesis of Biphenyls on Droplet Microarrays at Nanoliter Scale11Evaluating the green credentials of flow chemistry towards industrial applications1Transforming organic chemistry research paradigms: Moving from manual efforts to the intersection of automation and artificial intelligence5Organopalladium Catalysis as a Proving Ground for Data-Rich Approaches to Reaction Development and Quantitative Predictions8Novel solid-state synthesis of surfactant- and solvent-free Pd tetrahedron nanocatalysts7Enabling High Throughput Kinetic Experimentation by Using Flow as a Differential Kinetic Technique**10Enabling High Throughput Kinetic Experimentation by Using Flow as a Differential Kinetic Technique**0Automated approaches, reaction parameterisation, and data science in organometallic chemistry and catalysis: towards improving synthetic chemistry and accelerating mechanistic understanding20Combining Hammett σ constants for Δ-machine learning and catalyst discovery4Geometric deep learning-guided Suzuki reaction conditions assessment for applications in medicinal chemistry11How to actively learn chemical reaction yields in real-time using stopping criteria0Photocatalytic acylation of lysine screened using a microfluidic-based chemical robotic system6Direct Heterocycle C–H Alkenylation via Dual Catalysis Using a Palladacycle Precatalyst: Multifactor Optimization and Scope Exploration Enabled by High-Throughput Experimentation3Computational Methods Enable the Prediction of Improved Catalysts for Nickel-Catalyzed Cross-Electrophile Coupling41Chemoinformatic Catalyst Selection Methods for the Optimization of Copper–Bis(oxazoline)-Mediated, Asymmetric, Vinylogous Mukaiyama Aldol Reactions21Controlling Reactivity and Selectivity in the Mizoroki–Heck Reaction: High Throughput Evaluation of 1,5-Diaza-3,7-diphosphacyclooctane Ligands16Rapid reaction optimization by robust and economical quantitative benchtop 19F NMR spectroscopy12Combinatorial high throughput methodologies: the potentials in heterogeneous catalysts synthesis, screening and discovery—a review12Computationally Guided Ligand Discovery from Compound Libraries and Discovery of a New Class of Ligands for Ni-Catalyzed Cross-Electrophile Coupling of Challenging Quinoline Halides12An air- and moisture-stable ruthenium precatalyst for diverse reactivity28Palladium, [ N , N ′‐1,2‐ethanediylidenebis[2,6‐dimethylbenzenamine‐κN]][(3,4‐ η )‐2,5‐furandione] ( DMP DAB–Pd–MAH)0Bayesian optimization assisted screening conditions for visible light-induced hydroxy-perfluoroalkylation5Interfacing High-Throughput Electrosynthesis and Mass Spectrometric Analysis of Azines10Deciphering complexity in Pd–catalyzed cross-couplings19Recent Advances in Ligand-Controlled Regio- or Stereodivergent Transition-Metal-Catalyzed Hydroelementation (H[E]) (E = H, B, Si, Ge) of C–C Unsaturated Systems7From Characterization to Discovery: Artificial Intelligence, Machine Learning and High-Throughput Experiments for Heterogeneous Catalyst Design190Engineering a Sustainable Future: Harnessing Automation, Robotics, and Artificial Intelligence with Self-Driving Laboratories42Digital manufacturing of perovskite materials and solar cells12molli: A General Purpose Python Toolkit for Combinatorial Small Molecule Library Generation, Manipulation, and Feature Extraction11Facilitating catalytic research via better data reporting and curation: A case study of propane dehydrogenation on Ga/H-ZSM-52Rapid Exploration of Chemical Space by High-Throughput Desorption Electrospray Ionization Mass Spectrometry34Computational methods for asymmetric catalysis14Calibration-free quantification and automated data analysis for high-throughput reaction screening5Data efficient molecular image representation learning using foundation models5Digitalisation of catalytic processes for sustainable production of biobased chemicals and exploration of wider chemical space8Flow chemistry as a tool for high throughput experimentation15Highly efficient Fe 3 O 4 @Pd@C 3 TES catalysts for azide/nitroaromatic hydrogenation and Suzuki–Miyaura cross-coupling: the promotion of nano-porous triethoxypropylsilane as reaction cavities2Physically Interpretable Machine Learning Unveils a Universal Descriptor for High-Throughput Design of Single-Atom CO2 Reduction Catalysts0Reaction development: a student's checklist15Innovative Applications of Rotary Evaporators in Vacuum-assisted Synthesis for Sustainable Chemistry2Flash Thermal Racemization of Chiral Amine in Continuous Flow: An Exploration of Reaction Space Using DoE and Multivariate Transient Flow3Optimisation Strategies0Local reaction condition optimization via machine learning1MicroPhotoGas Reactor: High-Throughput Experimentation for Photoinduced Reactions under a Gas Atmosphere1Cyanomethylation of Aldehydes on an Electrochemical Microflow System and Utility of Machine Learning‐Assisted Examination of the Reaction Conditions6Exploring New Reactions with an Accessible High-throughput Screening (Open-HTS) Chemical Robotic System2Modeling and parametric study of benzyl thiocyanate synthesis via heterogeneous iron catalyst using artificial neural networks1A Scoring Model for Catalyst Informatics Based on Real-Time High-Throughput Fluorogenic Assay for Catalyst Discovery and Kinetic Profiling1Expeditious and Automated Dispensing of ChemBeads for High-Throughput Experimentation in 384-Well Microtiter Plates4Parallel Palladium-Catalyzed Synthesis of Carboxylic Acids from Aryl Iodides, Bromides, and Vinyl Triflates Using Acetic Anhydride and Formate Anion as an External Condensed Source of Carbon Monoxide0Production of Polymer Monomers through Integrated Catalytic Approaches3Machine learning application in thermal CO2 hydrogenation: catalyst design, process optimization, and mechanism insights13Advancing Organic Chemistry Using High‐Throughput Experimentation26Advancing Organic Chemistry Using High‐Throughput Experimentation7Liquid Crystal‐Driven Chemical Feeding Accelerates Condensation Reactions in Droplet Microreactors3Machine Learning for Accelerating Energy Materials Discovery: Bridging Quantum Accuracy with Computational Efficiency44Generalization of High-Throughput Experimentation in Organic Chemistry: Case Study on the Flortaucipir Synthesis0Solvent Sustainability in Drug Discovery: Where Are We Now, and How Can We Improve?25In Situ Generated Triazine Co-Catalyst Unlocks Amidine Arylation under Dual Nickel/Photoredox Catalysis: A Platform for Mild C–N Bond Formation2Synthesis of optically active target molecules0Fully automated and high-fidelity robotic platform enabling accelerated discovery of nanocatalysts2Elucidating the fundamental governing principles of CO 2 reduction on single-atom catalysts through interpretable machine learning6Sustainable chemistry in pharma: Pfizer green chemistry team's perspective0Taming the tiger: Bayesian optimization of organocatalyzed ring-opening polymerization in flow0

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  50. A reactivity model for oxidative addition to palladium enables quantitative predictions for catalytic cross-coupling reactions

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